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    • #660684

      Hi ladies!

      As crossdressers, we all strive to perfect our feminine image. We start feminizing our male bodies by shaving off all of our hair, moisturizing all over so that we’re soft and smooth, painting our finger- and toenails so that they’re pretty like real women have, and more. Then we modify our body shapes by padding and shapewear to get that wonderfully feminine silhouette we all desire, and we wear lingerie, dresses, hose, heels, makeup, jewelry, perfume, wigs and more so that we are seen as the women we want to be.

      But once we’ve done that, have we really passed as women?

      That leads me to this question: If you had the opportunity, once you were all dressed and made up and have transformed into your feminine self, would you go out on a date with a man? A real man that is, not one of our sisters in male mode.



    • #660692

      I know I’m the proverbial unicorn on CDH, but I want to CD solely for the purpose of getting a guy to date me. And…..


    • #660693

      No.  I love my wife and am crossdressing only because I love wearing feminine clothes.

    • #660711

      I have been on dates with a few men but I am very very picky about the type of man that I will go with I don’t want one of those big Burley and demanding types for me I like a type that while they’re still a man they do have some sense of compassion and ability to be polite and treat you well well groomed well kept but my preferred choice is to be with another CD in this category.

      • This reply was modified 2 years ago by Jasmine. Reason: Caught a grammar error
    • #660718
      Trish White

      Hi Holly, I did go out with a man. It only happened once and more or less by chance. He was very nice, a true gentleman and treated me like a lady. It was a very nice experience and one I often look back on, he made me feel very feminine.

      • #660719

        That is definitely the kind of man that I would be looking for a true gentleman who understands that we’re not a fetish were people congratulations

    • #660723

      No! Now that I have transitioned and live as a woman full time, I have no feelings or attractions for men. I definitely have attractions and feelings towards women! I know that I am a trans lesbian and quite happy with that. Dates with women in my life have been wonderful! 🙂

      Hugs girls,

      Lauren M

    • #660738
      Peggy Sue Williams
      Duchess - Annual

      Since I am happily married to a supportive spouse, I checked “no.”

      However, that being said, in earlier years, before I was married, there was a one time incident where I mixed cross dressing, alcohol, and kissing another male.  The incident gave me much to consider and think about.  In short, I never again mixed alcohol with cross dressing, and I realized that I am 100% heterosexual.

      OTHO, before I was married, I dated many women who made it a requirement that I cross dress for all our dates and assume the role of the female, but that is another story.


    • #660742

      God, i’m so wishy-washy.
      I used to be flat out no.
      Then a definite maybe.
      But now i’m a yes, please. As long as he’s nice to me like a proper gentleman should be.
      And they are hard to find so i’m not holding my breath.

      Thanks for asking.

    • #660791

      Absolutely not.  I have no mandate to go on a man-date.

    • #660801

      Sure, if I met one who was kind and caring, sensitive and considerate, who made me smile, laugh, and feel good about myself. Does such a man exist? But, I’m non-binary, so I think I could enjoy being with anyone with those traits, regardless of sex or gender.


    • #660807

      Hi Holly, I checked the “NO” box because I’m married.

      Now, if I wasn’t married, I would probably check the “I MIGHT” box. While I prefer the company of women far, far more than men, going out for dinner and a movie might be a fun experience. I often have men hold the door open for me going into stores and it feels quite nice. And I’ve had a few men flirt with me – a couple in a hardware store and another in a grocery store. They seemed nice enough guys. But of course, I’d be careful – no going to his place for drinks, I’d drive my own vehicle and meet somewhere instead of him picking me up in his vehicle, always be in a public place with other people around. I’m sure there is a safety guide to dating somewhere on the Internet.

      Thanks for the topic Holly, Hugs, Krista🐶

      • #660992
        skippy1965 Cynthia

        Kinda the same. Ten years ago the answer would have been definite and emphatic no, but now? I’m still attracted to women not men BUT if the right PERSON appears in my life then I think I’d be ok. As we ask others to acknowledge about ourselves, it’s the person inside who is most important not the outside appearance. ( i.e. it’s the gift not the wrapping paper that counts!)

    • #660835
      karley delaware
      Baroness - Annual

      Hi Holly……..There was an occasional customer at work that was very very nice to me …….and would always draw the soft side of me out.    When I started to grow my hair out ……………he would want to check the length ( out of view of my co-workers) .  He made a comment that he knew there is a girl in there….. somewhere…………………..since pandemic and change of hours ……..have not seen him ………….my hair is a lot longer ………down to mid back (kept in a pony tail or bun)………would love to show him …….yes….there is a girl here …………..(tears) …..I really really  miss him……………..would have gone on a date …….dressed!!!  He could draw the girl out of me and would love to be his girl……………………….karley

      • #661498

        Surely you’ve tried to find this wonderful guy!

    • #660871

      Where do you think of these, great question. I recently went on a date, my second. I was completely honest with my wife. She was supportive on both occasions.
      Also, being able to talk open about my experience during the date, how I felt, and what he wore, was my favorite part.
      Prior, a moment only reserved for girls. We sat up all night talking. Go figure, how cathartic. xoxo

    • #660891

      Dearest Holly
      My reply basically is going to upset a few girls here but i have no intention of going out with a Man as i am Straight!
      I would however enjoy the company of another girl if we strode out together!
      My big hope is to step out with another girl for drinks and have a girly chat as well!
      If we dance together later even better!
      To be up front i have never kissed another girl before and am something of a novice!
      Thanks again Holly for a wonderful Topic!
      Love & Hugs
      Anna xxxx

    • #660952

      I would like to but I wouldn’t cheat on my wife.

      Hugs, Liara

      • #660961

        Liara, I fully agree!

        I think that from the perspective of those of us who are happily married, we wouldn’t want to do anything that would cause problems in our marriage. But that doesn’t mean that we can’t wonder about what it would be like to go out with a real man!!!



    • #660998

      Yes, I definitely would if he is my type of man, that is handsome, well educated, a little romantic, financially stable, caring and respectful towards women.

    • #661027

      I’m single and would consider myself straight…at least as a guy. Is this resonating with anyone else? My feelings on this are a little different as a girl and I’d really be available to dates and possibly more with a man if he was considerate, charming, and we got a long. I look at it like an affirming experience for me that I’d like to have at least once.

      • #661046

        Yes, it does resonate with me. I feel the same way.

      • #718985

        Is agree.  As I have gone down my cd path there are moments when I get sept up in the moment and I find myself being more femme than just dressing.  My behavior and mannerisms change too. It is really quite surprising to me when that happens – in a good way.   Flattery really does go far.  Now if  I experienced these feelings in the presence of a guy, would I accept a request for a date – maybe?  Many things would have to fall into place for me to go out with a man when dressed.   Curiosity has led me far down this femme path of experiencing the female perspective and I could see my curiosity get the best of me if all things aligned.

        • #719019

          Be careful Celeste, it is a slippery slope and easy to fall down.  Once you do it is difficult to go back up.  I know.

    • #661033

      Not on your nelly! Men are awful. Sometimes I’m even trying not to be one.

      • #661047

        Sometimes I feel the same way.

    • #661058

      Guess I’m a lesbian!


      • #719893

        Update: I often go out with male friends… is that called a date… to go and drink beer on a hot day?


    • #661114

      I was considering the option, “I might, but am not sure” until the very end where the question finishes with, “A real man that is, not one of our sisters in male mode.”  After reading that I had to choose, “No” because I really don’t have an attraction to men.  Although the certain male physiques may be erotic, there isn’t that desire for a “real man.”

      • #661117

        I have only gone out with other CD friends in male mode.  The trust factor is much higher.  I shy away from most nonCd guys.  I have made a couple of exceptions.

    • #661122

      No, I wouldn’t go out with a man. I don’t need validation of who I am to be provided by “a real man”. (Or by an unreal man anyway).

    • #661378

      Yes of course if was single, because I have boyfriend but as gay couple.



    • #661442

      I absolutely would go out with a man.  If I can be taken in a date and treated like a lady, bring it on.  I might even kiss and tell about the experience. Treat me like a princess and let me show off my Venus!

    • #661464


      All hypothetical, since I’m happily married, I still don’t know if I could commit if I weren’t.

      My mind does wander, though, when the pink fog settles over me and I take on a more feminine exterior. I wonder what it’d be like to have a handsome gentleman woo me, knowing I still had my own male parts.

      Just going through with it would be hard, though.

      Much love,

    • #661491

      Wouldn’t be afraid to admit if I was gay but I know I’m not. The thought of being intimate with a man leaves me cold. So go on a date with a man-no.
      would go out as friends, buts would only date women.

      B x

    • #661500


      I just reread through a lot of these comments and I don’t see yours here. What would you do?


      • #661814

        Hi Gwyn.

        Oops, you’re right. Sometimes when I post these topics I forget to include my own response!

        Let me start by saying that when I’m in male mode, that would never, ever even be considered. However, when Holly comes out, then everything about me turns feminine, my dress, my mannerisms, my actions, my attitude, so that thinking of going on a date seems to be normal and natural. That’s what women and men do, right? And truth be told, if I was single, I definitely would! I’d love to be out in public on a man’s arm, being seen and treated as his date. However, since I’m not single and am very happily married, then that just remains a fantasy in my mind…


        • #719922

          Holly, the question you pose is a slam dunk yes for 98% of us given the right circumstance.  Like you, my bride of 54 years comes before anything.  If she gave the word there would be a clothes burning in the morning.  I can’t say I never looked another woman, I’m old, not dead.  But NEVER acted on it.  That being said , I have no attraction for a man sexually.  But I would like to think that being totally treated as a lady would be an experience I would like to have.  At my age, and size , I will never be considered feminine like most of my sisters so possibly I am missing a feeling  that you might already have.  Back to reality, I’m to scared to be seen by anyone, let alone Prince Charming.LOL

      • #719030

        Hi Gwyn, fair question.

        The short answer is that if I were not married, yes I would. However, I’m very happily married and would never do anything to jeopardize that, so the complete answer is no.



    • #661560

      An interesting question.

      I’m a private crossdresser so I don’t venture “out and about” in public, but IF that changes one day, and IF the man knows that I’m a CD, I would if I’m still single. 😉

      XOXO Rev

    • #661839
      Mary Priscilla
      Duchess - Annual

      I said yes, I would date a man as long as it was clearly specified that it would be social only. In fact, I have an open invitation to dine out with a wonderful gay man when it is pandemic safe to do so (he is severely health compromised). The other reason for being open to dating a man is that having a male escort would, hopefully, preclude any unwanted harassment.

      • #661904

        Mary Priscilla, you raise a great point. Being on the arm of a man would definitely help convey the image that we want to portray, that of being a real woman.


    • #669386

      You know, if I was all dressed totally as girl, from Pretty Lingerie to Lovely FEMININE dress or cute skirt and top outfit.


      As long as I’m treated like a girl on a date.

      • #669393

        A great intriguing question Holly. Honestly, yes, I think in time, I would. I think being completely enfemme changes your personality and your emotions. But this is what I think. As a complete newbie I’d have to experience it first. This is all ahead for me. I’d need professional help with makeup especially. Still, if the mood was right, a nice meal in a secluded restaurant, warm conversation at a nice hotel bar, a little intimate touching, maybe slow dancing. Who knows where the night might end? Why not. x

    • #669429

      When I first got into crossdressing, it was because of a guy I was dating. I always wanted to crossdress, but did not have a clue how to start, what to do, nothing. I met this guy, come to find out he crossdressed, and I knew I found my person to help me get started. We only dated for 6 months, but if it wasn’t for him, it would still be a dream instead of a reality. Now I have 2 female friends that help me in more ways than one, but I will never forget Tony helping me get started.

    • #669481

      The great debate!

      The more I dive into Catherine, the more I’m on the fence about this subject. When I first started dressing I considered myself a ‘cross-lesbian’ I liked and wanted to present more femme, but still only wanted to be with women both emotionally and sexually. The more I dressed and have gone deeper into Catherine, the more I wonder how it would be taken on a date with a man, let alone anything else that might transpire.

      Deep down I feel like I want to not only feel sexy/attractive, but I want others to feel that way towards me. Given my comfortableness and need/desire to dress, its only reasonable that when being Catherine that wanting men or women to see me as attractive or sexy is something that I also desire/need in my life.

      • #669486

        This is an interesting question for me. I would on one level like to experience that part of femininity. Although I am heterosexual, I have found the notion intriguing if you could turn the table on the socio-sexual expectations, and take on the female role with all that it entails if I may be so bold as to state. Crossdressed, and taking on the personality of my alter ego would indeed be a way to do that in some measure.
        It’s highly unlikely that it would ever happen, but often my fantasies will go there. If all the stars aligned however – and there’s a lot of stars to align – I think I would want to live it out.

    • #669694

      No, I would not. I love crossdressing. But I love my wife of 54 years more. Even though we are slowly walking through my being a cross dresser, I would not date another person; male or female.

    • #669700

      With my life situation, I have questioned myself even further. If some rich guy came to me and said, I saw your performance tonight. I fell in love with that girl, I want to know her. Then it became, I want you as my partner. Be mine. Don’t worry about work. I’ll take care of you. If anything happens to me, you’ll be okay. For life.
      now where was that arsenic again haha
      But seriously-as a guy I have no interest in guys except as friends. As a guy I’m a guy.
      As Triesste, I prefer to be called she. I try to be as close to a fully functioning woman as possible and that means interacting with men. I’ve been hit on more than once.
      It’s good experience-how to say no thanks without being a b+++h, or totally freezing up. I’m not a sex worker and no interest in coming across as one.
      Would I date a real man-yes, if it’s a real date and he’s not a real jerk.

    • #669815

      I’m bi. So it would be yes. I have done it long years ago with a divorced man in my younger 20s. We used to have a thing going. I’m not going into details here lol. But was all indoors and private.
      I used to dress up in sheer black night gown with lingerie underneath. Sometimes just throw several things to wear. Casual nothing sexy. just lipstick, camisole and a pair of ruffled pants.

      If I ran into the right man, and he was loving and caring and accepted me for who I truly am, then I would definitely like to go out in public with him.

    • #669857
      Fiona Black
      Baroness - Annual


      I voted no because I have no interest in men as far as dating or sex is concerned. However, if the guy was a friend or someone I knew extremely well, who accepted Fiona and who I knew had zero interest in me “that way” then it would be nice to be the female half of a typical date.

      • #719065

        Thanks Fiona, I agree with your comment, that would be the only way I would go out with a man. I do have male friends who know I am a trans woman and they’ve been fine to go for something to eat or out for coffee, I did go to a movie night with one good male friend, but there was also one of my gg girlfriends along with us.



        Ms. Lauren M

    • #718997

      Yes I would and have more than once. The dates have been mostly dinners and a movie or dancing. A couple times the man turned out to be less than a gentleman, but most have been caring and considerate. Some have even progressed to the intimate stage. If I wasn’t married, I could have seen a couple of them progressing to a LTR and more.

    • #719047

      Being single I have dated other men over the years but only men that know and appreciate that I am a CD and will treat me like a lady. It isnt enough to just dress as a woman but I do enjoy the full experience of completely falling into the role of my female self. It’s very comfortable being in public places like a movie or resturant with a date and enjoying the romance of kissing and having doors opened for you. I am totally a woman in actions behavior and mannerisms. The secret is finding that special guy that enjoys me as much as I enjoy him

    • #719058

      I’ve known I was bi since puberty so my answer is yes I would date a real man and I have in the past. I find some men very handsome and cute but I’m picky. A man who is respectful, clean, and treats me like a woman in every way is my kind of date but those kinds are few and far between.

    • #719075

      I wouldn’t rule it out.  There are some men I could be attracted to on that level, although not many.  I have always thought of myself as heterosexual but bi curious.  Once I put on a skirt, who knows?  XO – Julia

    • #719079

      While in man mode I have dated ladies that I was certain were crossdressing, and truly enjoyed the experience. So pretty sure I would date while en femme.

    • #719083

      Hi Holly, well, I must have missed this before so here goes

      If I were at least starting to transition.
      If I were single
      If I felt comfortable enough about myself
      If I felt comfortable enough about the man (accepting he was a gentleman)
      If this ‘first’ date was to some place mostly in public.

      And hoping he would show continuing interest after me ‘coming out’ –

      If all these ‘ifs’ worked out, and he asked again, I’d accept a second one.

      But sadly, all the above was some time ago.

      Hugs, ChloëC

    • #719147

      I had a relationship with a man as Michelle.  He was actually married, but was questioning his sexuality.  As someone who was presenting as a woman even with a male part, I was able to help him experiment.  He’s since then come out and left his wife.

    • #719252

      I would not for sure. I do love getting dressed up and feeling pretty and womanly, I am however not interested in Men at all. I love the feel of my dresses and girly clothes, my panties and bras when I am wearing them. I love to do my makeup when I get the chance and taking pictures. I have gotten into doing nails, not just painting them but actually doing dips and keeping them on. I am 100% committed to my loving wife of 20 years. She is fully supportive of me, we share clothes, bras, swimsuits. We will sit and do our makeup together, she buys me wigs and we bought a nail table for me to do our nails at home. While I do love being Syndee I do not see myself ever being interested in being with anyone other than my wife.

    • #719258

      No, I could not cheat on my wife.

      • #720516
        Janet Woodham
        Duchess - Annual

        That would have been my view too Julie until my wife passed away. I am not sure about dating now but if I do it will probably be with a man.

      • #720546

        Hi Julie.

        I fully understand your perspective and completely agree. And let me clarify, I am absolutely NOT advocating that anyone cheat on their spouse. I’ve said it before in numerous places and will say it again, I am happily married and would never, EVER cheat on my wife! You may not know this, but my poll questions are designed to stimulate discussion and help others talk about things they may have thought about, but not brought out into the open. They are not ever suggesting doing anything that would jeopardize a relationship.



    • #719911

      Don’t take this the wrong way, Holly as it is not a criticism. I see what you mean in a way but find the language ambiguous.

      When I am in ‘male mode’ (masculine presentation; I am always male regardless of my present gender) I am a very thoroughly man. If I were to date a Masculine-to-Feminine cross-dresser it would be because, as a male, I am attracted to femininity. She, being attractively feminine and attractive to me, I would tend to view her as a real woman.

      Being a man is not equivalent to being male nor is being a woman the same as being female. For example, a cow is female, not a woman. A Peacock is male, but not a man and its masculinity (in human terms) is questionable.

      It is the authenticity of the presentation that is important to me not necessarily the effectiveness of the representation. A male who is delightfully feminine in a mature and sophisticated manner is lovelier to me than many females of greater, conventional allure.

      There is nothing contradictory in a male wanting to be a woman and, if authentically a woman, learning to be a lady and, having learned to be a lady, being properly treated as such.


    • #720556
      Sherri Remington
      Duchess - Annual

      Holly to me that would be the icing on the cake in becoming the woman that I’m trying to present. What a thrill it would be for a man to want to go on a date with me knowing I was not a woman but wanting to be with me anyhow. WOW!


    • #720561

      I would love to and I think about it all the time. What I would wear, where we would go.. etc.. But I would be too scared to actually do it!

      • #720565

        That’s why dates always start a half hour late.

      • #720587
        Janet Woodham
        Duchess - Annual

        I know exactly what you mean Serena.

    • #720803

      Over the years I had a couple of relationships with men.  It feels so wonderful to be a woman in a relationship it is so fulfilling.   I do not regret either relationship and if I find someone that I was attracted to I would certainly try to develop a relationship with them.

    • #720955
      Wendie Cross

      I’m not the kind to kiss and tell, but yes I absolutely would. Being a bisexual male my perfect relationship would be being in love with another crossdresser like myself. (just being honest)

    • #724885

      I want to comment, and I hope it’s not taken as being mean or patronizing at all, I really just want it to be helpful. I’ve been reading through the comments-now I have not lived in the Western world for a long time, and I have dated in Japan my country of residence, but not lately. That said, I am seeing comments that suggest dating is an automatic ticket to a night of X-rated abandon. That is not dating. It sounds more like being an escort-which is fine, but different. Two points to consider-purpose. Why are you there? talk to your date. Boundaries-what is and is not okay? talk to your date. It’s like any relationship, communication counts-for everyone. Have an amazing experience, and get home safe.
      Wishing you all happiness and fulfillment.

    • #725046

      Hi Holly,

      Yes. Absolutely.

      As you say, we put all this time, money and immense effort into transforming. I didn’t realize once I had taken all those steps to get there that it would lead to the next, wanting to be desired by a man. And it took an enormous amount of self-reflection to realize this part of me and then accept that is who I am. I have my own caveats and it will only happen under the right circumstances, but I would love to go on a date with a man.



      • #725343
        Janet Woodham
        Duchess - Annual

        Hi Felicia,

        This has been my experience to too and it has not been comfortable and is still ongoing. Anything that happens will be when it is right for me and on my terms.

        • #725346

          Hi Janet.  It’s always good to hear from you.

    • #725189

      I have gone on a date as Jessica a couple of times before I was married.  Whenever I dress it brings out my attraction to men.  I just want that male energy when I’m dressing.  I want to be held and dominated and treated like a prize while we are on the date and a toy at the end of it haha.  It really helps with my desire to feel feminine.

    • #726321

      In my case I have a boyfriend and it’s incredible! It’s incredibly exciting to be in a relationship with a guy and if anyone wants to know details, feel free to message me!

    • #727487

      As a heterosexual man I wouldn’t consider dating a man but I do have to admit that the idea of dating man as a woman is a strong and recurring fantasy for me, although it’s not so much the date part but the after being out together part.

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